WO2022056096A1 - Matériau d'interface thermique - Google Patents

Matériau d'interface thermique Download PDF

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Publication number
WO2022056096A1
WO2022056096A1 PCT/US2021/049615 US2021049615W WO2022056096A1 WO 2022056096 A1 WO2022056096 A1 WO 2022056096A1 US 2021049615 W US2021049615 W US 2021049615W WO 2022056096 A1 WO2022056096 A1 WO 2022056096A1
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WIPO (PCT)
Prior art keywords
kit
epoxy resin
polyurethane prepolymer
thermally conductive
blocked polyurethane
Prior art date
Application number
PCT/US2021/049615
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English (en)
Inventor
Sergio Grunder
Marcel ASCHWANDEN
Tomonori Takahashi
Andreas Lutz
Original Assignee
Ddp Specialty Electronic Materials Us, Llc
DDP Specialty Products Japan K.K.
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Publication date
Application filed by Ddp Specialty Electronic Materials Us, Llc, DDP Specialty Products Japan K.K. filed Critical Ddp Specialty Electronic Materials Us, Llc
Priority to JP2023516572A priority Critical patent/JP2023550229A/ja
Priority to CN202180062398.XA priority patent/CN116057146A/zh
Priority to KR1020237008862A priority patent/KR20230069928A/ko
Priority to US18/025,545 priority patent/US20230323174A1/en
Priority to EP21789910.3A priority patent/EP4211198A1/fr
Publication of WO2022056096A1 publication Critical patent/WO2022056096A1/fr

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    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
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    • C—CHEMISTRY; METALLURGY
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    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
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    • C08G18/72—Polyisocyanates or polyisothiocyanates
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    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
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    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
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    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
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    • C08G18/72—Polyisocyanates or polyisothiocyanates
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    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
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    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
    • C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
    • C08G59/063—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with epihalohydrins
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    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
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    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
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    • C09J175/08—Polyurethanes from polyethers
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    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/08—Materials not undergoing a change of physical state when used
    • C09K5/14—Solid materials, e.g. powdery or granular
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/60—Heating or cooling; Temperature control
    • H01M10/61—Types of temperature control
    • H01M10/613—Cooling or keeping cold
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/60—Heating or cooling; Temperature control
    • H01M10/65—Means for temperature control structurally associated with the cells
    • H01M10/653—Means for temperature control structurally associated with the cells characterised by electrically insulating or thermally conductive materials
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    • C09J2301/00—Additional features of adhesives in the form of films or foils
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    • C09J2475/00—Presence of polyurethane
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

Definitions

  • the present invention relates to the field of two-component thermal interface materials.
  • thermal interface materials are needed.
  • Battery cells produce heat during charging and discharging operations.
  • the cells need to be kept in the right operating temperature (preferably 25-40°C) not to lose efficiency.
  • overheating can start a dangerous thermal runaway reaction. For that reason active cooling is commonly used.
  • cooled water glycol mixtures are pumped through channels that cool the metal bottom plate on which the battery cells/modules are placed.
  • thermal interface materials are employed.
  • the thermal interface materials (TIMs) need to thermally connect the modules with the cooling plate, meaning they must have a high thermal conductivity of > 2 W/mK.
  • Such elevated thermal conductivities can be achieved by formulating a polymeric matrix, such as epoxy, with high amounts (typically > 50 wt%) of thermally conductive fillers such as aluminum hydroxide, aluminum oxide, as disclosed in WO2014047932A1 .
  • the TIM serves a dual role of providing thermal conductivity for cooling and also mechanical fixation of the battery modules to protect them and keep them in place.
  • high lap shear strengths and cohesive failure modes are needed, so that long term fatigue tests are passed. This renders the battery system robust even after extensive dynamic vibration exposures.
  • the invention provides a kit for a two-component thermally conductive adhesive formulation comprising:
  • (b1) a nucleophilic cross-linker capable of reacting with the blocked polyurethane prepolymer (a1) and the aromatic epoxy resin (a2);
  • (b2) a catalyst capable of promoting the reaction of nucleophile (b1 ) with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2); wherein Part (A) and/or Part (B) further comprise a thermally conductive filler, and Parts (A) and (B) are designed to be blended together prior to use.
  • the invention provides a cured thermally conductive adhesive, resulting from mixing Parts (A) and (B) and allowing curing to occur.
  • the invention provides a battery assembly comprising battery modules fixed in place in the assembly by a cured adhesive composition resulting from mixing Parts (A) and (B), and/or mechanical fastening means, such that the adhesive composition provides thermal conductivity between the battery modules and a cooling substrate.
  • the invention provides a method for assembling a battery assembly, comprising the steps:
  • thermally conductive adhesive thermal conductivity of > 2 W/mK
  • addition of an aromatic epoxy resin and an epoxy silane in combination with a blocked polyurethane prepolymer leads to high cohesive failure mode at lap shear strengths higher than 0.8 MPa, as well as good fatigue performance.
  • the invention provides a kit for a two-component thermally conductive adhesive formulation comprising:
  • (b1) a nucleophilic cross-linker capable of reacting with the blocked polyurethane prepolymer (a1) and the aromatic epoxy resin (a2);
  • (b2) a catalyst capable of promoting the reaction of nucleophile (b1 ) with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2); wherein Part (A) and/or Part (B) further comprise a thermally conductive filler, and parts (A) and (B) are designed to be blended together prior to use.
  • the thermally conductive filler is not particularly limited.
  • thermally conductive fillers are those that have a coefficient of thermal conductivity that is greater than 5 W/m°K, greater than 10 W/m°K, or greater than 15 WZ m°K.
  • thermally conductive fillers include alumina, alumina trihydrate or aluminum trihydroxide, silicon carbide, boron nitride, diamond, and graphite, or mixtures thereof. Particularly preferred are aluminium trihydroxide (ATH), and aluminium oxide, with ATH being the most preferred.
  • the thermally conductive filler has a broad particle size distribution characterized by a ratio of D901 D50 of at or about 3 or more.
  • the thermally conductive filler is ATH or aluminium oxide having a broad particle size distribution characterized by a ratio of D901 D50 of at or about 3 or more, most preferably ATH.
  • thermally conductive fillers having a bimodal particle size distribution are also preferred. A bimodal distribution is when, for example, the ratio D901 D50 is at or about 3 or more, more preferably at or about 5 or more, more particularly preferably at or about 9 or more.
  • particles having a D50 of 5 to 20 microns and a D90 of 70 to 90 microns particularly a D50 of 7-9 microns and a D90 of 78-82 microns.
  • Particle size can be determined using laser diffraction.
  • a suitable solvent is deionized water containing a dispersion aid, such as Na4P2O? x 10 H2O, preferably at 1 g/l.
  • a dispersion aid such as Na4P2O? x 10 H2O, preferably at 1 g/l.
  • aluminium oxide and ATH having a bimodal distribution particularly ATH.
  • the thermally conductive filler is preferably present in the final adhesive at a concentration that gives a thermal conductivity of at or about 2.0 W/mK or more, preferably at or about 2.5 or more, more preferably at or about 2.8 or more, even more preferably at or about 2.9 or more, and most preferably at or about 3.0 or more.
  • this generally requires a concentration of thermally conductive filler of greater than 50 wt%, more preferably greater than 60 wt%, more particularly preferably greater than 70 wt%.
  • the thermally conductive filler is present at greater than 80 wt%.
  • the thermally conductive filler content in the final adhesive is less than 93 wt%, as higher levels can affect the adhesive strength and impact resistance negatively.
  • the thermally conductive filler is present at 85-90 wt%.
  • the thermally conductive filler may be present in Part (A), Part (B) or both. In a preferred embodiment it is present in both Part (A) and Part (B), as this reduces the amount of mixing required to properly distribute the thermally conductive filler when Parts (A) and (B) are mixed. Preferably it is present at similar or the same concentration in both Parts (A) and (B). In a particularly preferred embodiment it is present at 85-90 wt% in the final mixture of Parts (A) and (B), based on the total weight of the mixture. Preferably it is present both Parts (A) and (B) at 85 wt%.
  • the thermally conductive filler is ATH having a ratio D901 D50 of at or about 8 or more, used at a concentration of 85- 89 wt% in both Parts (A) and (B), based on the total weight of Part (A) or Part (B).
  • Part (A) of the adhesive composition comprises a blocked polyurethane prepolymer which is the reaction product of a polyisocyanate with a polyol, capped with a phenol, preferably 70-85 wt% aromatic polyisocyanate with 15- 25 wt% phenol.
  • the reaction is carried out with a tin catalyst.
  • the polyisocyanate may be aliphatic, aromatic, or a mixture, with aromatic polyisocyanates being preferred.
  • aromatic polyisocyanates include methylene diphenyl diisocyanate (MDI), toluene diisocyanate (TDI), p- phenylene diisocyanate (PPDI), and naphthalene diisocyanate (NDI), all of which can be reacted with a polyol.
  • MDI methylene diphenyl diisocyanate
  • TDI toluene diisocyanate
  • PPDI p- phenylene diisocyanate
  • NDI naphthalene diisocyanate
  • Particularly preferred is toluene diisocyanate (TDI), reacted with a polyol.
  • the polyol preferably is a polyether polyol.
  • the polyol may have two or more OH groups.
  • polyether polyols include poly(alkylene oxide)diols, wherein the alkylene group is C2-C6, particularly preferably the alkylene group is C2-C4.
  • suitable polyols include poly(ethylene oxide)diol, polypropylene oxide)diol, poly(tetramethylene oxide)diol. Particularly preferred is polypropylene oxide)diol, particularly polypropylene glycol).
  • reaction product of an aromatic diisocyanate with a polyether polyol in particular those listed above, and then capping with a phenol.
  • the phenol used for capping is preferably a phenol of the following formula: where R is a saturated or unsaturated C15 chain, particularly preferably R is a saturated C15 chain.
  • a polyisocyanate made by reacting TDI with a polypropylene oxide)diol, in particular when the resulting polyisocyanate has an equivalent weight of at or about 950.
  • the phenol-containing compound typically has a linear hydrocarbon attached to the phenol group to provide some aliphatic characteristics to the compound.
  • the linear hydrocarbon preferably includes 3 or more carbon atoms, more preferably 5 or more carbon atoms, even more preferably 8 or more carbon atoms, and most preferably 10 or more carbon atoms.
  • the linear hydrocarbon preferably includes at or about 50 or less carbon atoms, at or about 30 or less carbon atoms, at or about 24 or less carbon atoms, or at or about 18 or less carbon atoms.
  • a particularly preferred phenol is cardanol.
  • the blocked polyurethane prepolymer is made by reacting toluene diisocyanate with a polyether polyol, having an NCO content of at or about 4 - 5% and an equivalent weight of at or about 500 - 1500 g/eq.
  • the blocked polyurethane prepolymer is made by reacting an aromatic polyisocyanate based on toluene diisocyanate with cardanol, preferably 70-85 wt% TDI-based polyisocyanate with 15-25 wt% cardanol.
  • the reaction is carried out with a tin catalyst.
  • the blocked polyurethane prepolymer (a1 ) is preferably present in Part (A) at a concentration of 0.5 to 5 wt%, more preferably at 1 to 3 wt%, particularly preferably at 1 .5 to 2.2 wt%, based on the total weight of Part (A).
  • the blocked polyurethane prepolymer is made by reacting TDI with a polypropylene oxide)diol, in particular when the resulting polyisocyanate has an equivalent weight of at or about 950, and capping with cardanol, at 1 .5 to 2.2 wt%, preferably at or about 2 wt%, based on the total weight of Part (A).
  • Parts (A) and (B) are mixed prior to or simultaneously with application to a substrate.
  • the concentration of the blocked polyurethane prepolymer in the final, mixed adhesive can be calculated from the proportions of Parts (A) and (B) used to make the final mixed adhesive.
  • Parts (A) and (B) are mixed in a 1 :1 ratio by volume, in which case the concentration of the blocked polyurethane prepolymer in the final adhesive will be half the value in Part (A).
  • Aromatic epoxy resin (a2) is Aromatic epoxy resin (a2)
  • Part (A) comprises an aromatic epoxy resin.
  • the aromatic epoxy resin is preferably a reaction product of a diphenol with epichlorohydrin.
  • suitable diphenols include bisphenol A, bisphenol F, with bisphenol A being particularly preferred.
  • the aromatic epoxy resin is a reaction product of epichlorohydrin and bisphenol A, having the following characteristics:
  • the aromatic epoxy resin is preferably present in Part (A) at a concentration of 0.3 to 2 wt%, more preferably at 0.6 to 1 .5 wt%, particularly preferably at 1 to 1.2 wt%, based on the total weight of Part (A).
  • the aromatic epoxy resin is a reaction product of epichlorohydrin and bisphenol A, having the following characteristics: at 1 to 1 .2 wt%, based on the total weight of Part (A).
  • Parts (A) and (B) are mixed prior to or simultaneously with application to a substrate.
  • the concentration of the aromatic epoxy resin in the final, mixed adhesive can be calculated from the proportions of Parts (A) and (B) used to make the final mixed adhesive.
  • Parts (A) and (B) are mixed in a 1 :1 ratio by volume, in which case the concentration of the aromatic epoxy resin in the final adhesive will be half the value in Part (A).
  • Part (A) comprises an epoxy silane.
  • An epoxy silane is any molecule that bears a di- or trialkoxy silane moiety bonded to an epoxy moiety.
  • Suitable epoxy silanes are of the formula: where R 1 , R 2 and R 3 are independently selected from C1-C3 alkyl, and R 4 is a divalent organic radical.
  • R 1 , R 2 and R 3 are independently selected from ethyl and methyl, with methyl being preferred, particularly when R 1 , R 2 and R 3 are methyl.
  • R 4 is preferably selected from alkylene, preferably C2-C12 alkylene, more preferably C2-C6 alkylene, particularly preferably propylene.
  • the epoxy silane is gamma- glycidoxypropyltrimethoxysilane.
  • the epoxy silane is preferably present in Part (A) at 0.2 to 0.75 wt%, more preferably 0.25 to 0.6 wt%, particularly preferably at or about 0.5 wt%, based on the total weight of Part (A).
  • the epoxy silane is gamma- glycidoxypropyltrimethoxysilane at 0.2 to 0.75 wt%, more preferably 0.25 to 0.6 wt%, particularly preferably at or about 0.5 wt%, based on the total weight of Part (A).
  • Parts (A) and (B) are mixed prior to or simultaneously with application to a substrate.
  • the concentration of the epoxy silane in the final, mixed adhesive can be calculated from the proportions of Parts (A) and (B) used to make the final mixed adhesive.
  • Parts (A) and (B) are mixed in a 1 :1 ratio by volume, in which case the concentration of the epoxy silane in the final adhesive will be half the value in Part (A).
  • Part (B) comprises a nucleophilic cross-linker capable of reacting with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2).
  • the nucleophilic cross-linker is preferably a di- or tri-amine, with triamines being preferred.
  • the amine groups may be independently secondary or primary, with primary being preferred.
  • the nucleophilic cross-linker preferably has a molecular weight of 1 ,500 to 4,000 Da, more preferably 2,000 to 3,500 Da, with at or about 3,000 Da being particularly preferred.
  • the nucleophilic cross-linker preferably has a backbone based on poly(alkylene oxide)diols, particularly C2-C6 alkylene, more particularly C2-C4 alkylene, with C3 alkylene being most preferred.
  • the backbone is based on a polyether of propylene glycol.
  • the nucleophilic cross-linker is a triamine having primary amines for greater than 90 % of amine groups, a molecular weight of at or about 3,000 Da, and a backbone based on a polyether of propylene glycol.
  • the nucleophilic cross-linker is a trifunctional polyether amine of approximately 3000 molecular weight, having the following characteristics:
  • the nucleophilic cross-linker is preferably present in Part (B) at a concentration of 0.1 to 10 wt%, 1 to 5 wt%, more preferably 1 .5 to 3.3 wt%, particularly preferably at 3 to 3.2 wt%, based on the total weight of Part (B).
  • the nucleophilic cross-linker is a trifunctional polyether amine of approximately 3000 molecular weight, having the following characteristics: at 3-3.2 wt%, based on the total weight of Part (B).
  • Parts (A) and (B) are mixed prior to or simultaneously with application to a substrate.
  • concentration of the nucleophilic cross-linker in the final, mixed adhesive can be calculated from the proportions of Parts (A) and (B) used to make the final mixed adhesive.
  • Parts (A) and (B) are mixed in a 1 :1 ratio by volume, in which case the concentration of the nucleophilic cross-linker in the final adhesive will be half the value in Part (A).
  • Part (B) comprises a catalyst capable of promoting the reaction of nucleophile (b1 ) with the blocked polyurethane prepolymer (a1) and the aromatic epoxy resin (a2).
  • the catalyst is preferably selected from Lewis bases and Lewis acids.
  • Preferred are tertiary amines, including diazabicyclo[2.2.2]octane, 2,4,6- tris((dimethylamino)methyl)phenol, DMDEE (2,2'-Dimorpholinodiethylether), imidazoles, such as 4-methylimidazole), triethanolamine, polyethyleneimine.
  • organotin compounds such as dioctyltindineodecanoate, and other metal catalysts such as tetrabutyltitanate, zirconium acetylacetonate, and bismuthneodecanoate.
  • organotin compounds such as dioctyltindineodecanoate, and other metal catalysts such as tetrabutyltitanate, zirconium acetylacetonate, and bismuthneodecanoate.
  • metal catalysts such as tetrabutyltitanate, zirconium acetylacetonate, and bismuthneodecanoate.
  • diazabicyclo[2.2.2]octane is particularly preferred.
  • the catalyst is preferably used at 0.05 to 0.2 wt%, more preferably 0.075 to 0.15 wt%, more particularly preferably at or about 0.1 wt%, based on the total weight of Part (B).
  • Parts (A) and (B) may additionally comprise other ingredients such as:
  • Plasticizers such as esters of unsaturated fatty acids, in particular C - Ci8 fatty acids, in particular methyl esters, tris(2-ethylhexyl)phosphate;
  • Stabilizers such as polycapralactone
  • Fillers other than the thermally conductive filler, such as carbon black, calcium carbonate, glass fibres, wollastonite;
  • Viscosity reducers such as hexadecyltrimethoxysilane.
  • the invention also provides a cured thermally conductive adhesive, resulting from mixing Parts (A) and (B) and allowing curing to occur.
  • Parts (A) and (B) may be mixed in any proportion.
  • Preferably the final concentrations of the ingredients fall within the following ranges after mixing (A) and (B): Application to substrate
  • Parts (A) and (B) are mixed and can be applied to a substrate using known methods, such as a manual application system or in an automated way with a pump system using 201 pails or 200 I drums or any other preferred container.
  • the cured adhesive composition is characterized by a thermal conductivity, measured according to ASTM 5470-12 (as described in the Examples), of about 2.0 W/mK or more (preferably at or about 2.5 or more, more preferably at or about 2.8 or more, even more preferably at or about 2.9 or more, and most preferably at or about 3.0 or more).
  • the cured adhesive composition preferably has a lap shear strength, according to DIN EN 1465:2009, as measured in the Examples, of greater than 0.7 MPa, more preferably greater than 0.8 or 0.9 MPa.
  • the two-part composition cures at room temperature (preferably as characterized by an increase in a press-in force of about 100% or more, after aging for 24 hours after mixing).
  • the invention also provides a battery assembly comprising battery modules fixed in place in the assembly by a cured adhesive composition and/or by mechanical fastening means, resulting from mixing Parts (A) and (B), such that the mixture, when cured, provides thermal conductivity between the cells and the substrate.
  • Parts (A) and (B) are mixed in the desired ratio, and the mixture is applied, before curing, in a manner to separate the battery cells physically and electrically and to fix the cells in place on a substrate designed to cool the cells, such that the mixture, when cured, provides thermal conductivity between the cells and the substrate.
  • the thermal conductivity of the adhesive in the assembly is preferably 2.0 W/mK or more, more preferably at or about 2.5 or more, more particularly preferably at or about 2.8 or more.
  • a kit for a two-component thermally conductive adhesive formulation comprising:
  • (b1) a nucleophilic cross-linker capable of reacting with the blocked polyurethane prepolymer (a1) and the aromatic epoxy resin (a2);
  • (b2) a catalyst capable of promoting the reaction of nucleophile (b1 ) with the blocked polyurethane prepolymer (a1) and the aromatic epoxy resin (a2); wherein Part (A) and/or Part (B) further comprise a thermally conductive filler, and parts (A) and (B) are designed to be blended together prior to use, and wherein the blend has a thermal conductivity of greater than 2.0 W/mK.
  • a kit according to embodiment 1 comprising:
  • (b1 ) a nucleophilic cross-linker capable of reacting with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2);
  • Part (b2) a catalyst capable of promoting the reaction of nucleophile (b1 ) with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2); wherein Part (A) and/or Part (B) further comprise a thermally conductive filler, which is aluminium trihydroxide, and parts (A) and (B) are designed to be blended together prior to use.
  • a thermally conductive filler which is aluminium trihydroxide
  • (b1 ) a nucleophilic cross-linker capable of reacting with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2);
  • Part (b2) a catalyst capable of promoting the reaction of nucleophile (b1 ) with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2); wherein Part (A) and/or Part (B) further comprise a thermally conductive filler, and parts (A) and (B) are designed to be blended together prior to use, and wherein the thermally conductive filler is present at between 60-90 wt%, based on the total weight of the blend.
  • (b1 ) a nucleophilic cross-linker capable of reacting with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2);
  • (b2) a catalyst capable of promoting the reaction of nucleophile (b1 ) with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2); wherein Part (A) and/or Part (B) further comprise a thermally conductive filler, and parts (A) and (B) are designed to be blended together prior to use.
  • (b1 ) a nucleophilic cross-linker capable of reacting with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2);
  • (a3) an epoxy silane which is of the formula: where R 1 , R 2 and R 3 are independently selected from C1-C3 alkyl, and R 4 is a divalent organic radical;
  • (b1 ) a nucleophilic cross-linker capable of reacting with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2);
  • (b2) a catalyst capable of promoting the reaction of nucleophile (b1 ) with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2); wherein Part (A) and/or Part (B) further comprise a thermally conductive filler, and parts (A) and (B) are designed to be blended together prior to use.
  • (b1 ) a nucleophilic cross-linker which is a di- or tri-amine, with the amine groups being primary or secondary; (b2) a catalyst capable of promoting the reaction of nucleophile (b1 ) with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2); wherein Part (A) and/or Part (B) further comprise a thermally conductive filler, and parts (A) and (B) are designed to be blended together prior to use.
  • (b1 ) a nucleophilic cross-linker capable of reacting with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2);
  • a catalyst selected from Lewis bases and Lewis acids, preferred are tertiary amines, including diazabicyclo[2.2.2]octane, 2,4,6- tris((dimethylamino)methyl)phenol, DMDEE (2,2'-
  • Part (A) and/or Part (B) further comprise a thermally conductive filler, and parts (A) and (B) are designed to be blended together prior to use.
  • (b2) a catalyst capable of promoting the reaction of nucleophile (b1 ) with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2); wherein Part (A) and/or Part (B) further comprise a thermally conductive filler, and parts (A) and (B) are designed to be blended together prior to use.
  • (a1 ) a blocked polyurethane prepolymer which is the reaction product of an aromatic polyisocyanate produced by reacting an aromatic diisocyanate with a polyether polyol and capping with a phenol;
  • (a3) an epoxy silane which is of the formula: where R 1 , R 2 and R 3 are independently selected from C1-C3 alkyl, and R 4 is a divalent organic radical;
  • nucleophilic cross-linker which is a di- or tri-amine, with the amine groups being primary or secondary;
  • a catalyst selected from Lewis bases and Lewis acids, preferred are tertiary amines, including diazabicyclo[2.2.2]octane, 2,4,6- tris((dimethylamino)methyl)phenol, DMDEE (2,2'-
  • Part (A) and/or Part (B) further comprise a thermally conductive filler, and parts (A) and (B) are designed to be blended together prior to use.
  • Part (A) 0.5 to 5 wt%, based on the total weight of Part (A), of a blocked polyurethane prepolymer which is the reaction product of a polyisocyanate with a phenol;
  • (b1 ) a nucleophilic cross-linker capable of reacting with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2);
  • (b2) a catalyst capable of promoting the reaction of nucleophile (b1 ) with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2); wherein Part (A) and/or Part (B) further comprise a thermally conductive filler, and parts (A) and (B) are designed to be blended together prior to use.
  • (b1 ) a nucleophilic cross-linker capable of reacting with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2); (b2) a catalyst capable of promoting the reaction of nucleophile (b1 ) with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2); wherein Part (A) and/or Part (B) further comprise a thermally conductive filler, and parts (A) and (B) are designed to be blended together prior to use.
  • (b1 ) a nucleophilic cross-linker capable of reacting with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2);
  • (b2) a catalyst capable of promoting the reaction of nucleophile (b1 ) with the blocked polyurethane prepolymer (a1 ) and the aromatic epoxy resin (a2); wherein Part (A) and/or Part (B) further comprise a thermally conductive filler, and parts (A) and (B) are designed to be blended together prior to use.
  • (B) a second part, comprising: (b1) 1 to 5 wt%, based on the total weight of Part (B), of a nucleophilic cross-linker capable of reacting with the blocked polyurethane prepolymer (a1) and the aromatic epoxy resin (a2);
  • (b2) a catalyst capable of promoting the reaction of nucleophile (b1 ) with the blocked polyurethane prepolymer (a1) and the aromatic epoxy resin (a2); wherein Part (A) and/or Part (B) further comprise a thermally conductive filler, and parts (A) and (B) are designed to be blended together prior to use.
  • (b1) a nucleophilic cross-linker capable of reacting with the blocked polyurethane prepolymer (a1) and the aromatic epoxy resin (a2);
  • Part (b2) 0.05 to 0.2 wt%, based on the total weight of Part (B), of a catalyst capable of promoting the reaction of nucleophile (b1) with the blocked polyurethane prepolymer (a1) and the aromatic epoxy resin (a2); wherein Part (A) and/or Part (B) further comprise a thermally conductive filler, and parts (A) and (B) are designed to be blended together prior to use.
  • Part (A) 0.25 to 0.6 wt%, based on the total weight of Part (A);
  • nucleophilic cross-linker which is a trifunctional polyether amine of approximately 3000 molecular weight, having the following characteristics: at 3-3.2 wt%, based on the total weight of Part (B).;
  • Part (b2) a catalyst which is diazabicyclo[2.2.2]octane at 0.05 to 0.2 wt%; wherein Part (A) and/or Part (B) further comprise a thermally conductive filler, which is ATH having a ratio D90 1 D50 of at or about 8 or more, and its concentration is 85-90 wt% when Parts (A) and (B) are blended together.
  • a thermally conductive filler which is ATH having a ratio D90 1 D50 of at or about 8 or more, and its concentration is 85-90 wt% when Parts (A) and (B) are blended together.
  • thermoly conductive filler is ATH having a ratio D90 1 D50 of at or about 8 or more.
  • thermoly conductive filler is present in Part (A), Part (B) or both such that its concentration is 85-90 wt% when Parts (A) and (B) are blended together.
  • a kit according to any one preceding embodiment which further comprises a plasticizer in Part (A), Part (B) or both.
  • a cured adhesive made by mixing Parts (A) and (B) according to any one preceding embodiment, and allowing the mixture to cure.
  • a battery assembly comprising battery modules fixed in place in the assembly by a cured adhesive composition resulting from mixing Parts (A) and (B), according to any one preceding embodiment, and/or mechanical fastening means, such that the adhesive composition provides thermal conductivity between the battery modules and a cooling substrate.
  • a method for assembling a battery assembly comprising the steps:
  • GF200 is the reaction product of Aromatic polyisocyanate A and Cardanol. Reaction procedure: Cardanol (22.1 wt%) and Aromatic polyisocyanate A (77.85 wt%) were heated in a reactor to 60°C. Dibutyltin dilaurate catalyst (0.05 wt%) was then added. The reaction mixture was stirred for 45 min at 80°C under an atmosphere of nitrogen and then for 10 min under vacuum. The colourless reaction product was then cooled to RT and transferred into a container.
  • Diamine A is a member of a family of polyamines having repeat oxypropylene units in the backbone. As shown by the above structure, Diamine A is a difunctional primary amine with an average molecular weight of approximately 2000. Its amine groups are located on secondary carbon atoms at the ends of an aliphatic polyether chain. Triamine A [nucleophilic cross-linker (b1)]
  • Triamine A is a trifunctional polyether amine of approximately 3000 molecular weight. It has the following characteristics: ATH [thermally conductive filler]
  • the experimental formulations were prepared by mixing the ingredients listed in Table 2 on a planetary mixer or on a dual asymmetric centrifuge. In a first phase the liquid phases were mixed before the solid material is added to the formulation. The formulation was mixed for ca 30 min under vacuum before being filled into cartridges, pails, or drums.
  • the A and B components of the adhesive were mixed 1 :1 by volume with a static mixer and applied from a manual cartridge system.
  • Press-in force was measured with a tensiometer (Zwick).
  • the adhesive material was placed on a metal surface.
  • An aluminium piston with 40 mm diameter is placed on top and the material is compressed to 5 mm (initial position).
  • the material was then compressed to 0.3 mm with 1 mm/s velocity and force deflection curve was recorded.
  • the force (N) at 0.5 mm thickness is then reported in Table 2 and considered as the press-in force.
  • Thermal conductivity was measured according to ASTM 5470-12 on a thermal interface material tester from ZFW Stuttgart. The tests were performed in Spaltplus mode at a thickness of between 1 .8 - 1.2 mm. The described thermal interface material was considered as Type I (viscous liquids) as described in ASTM 5470-12. The upper contact was heated to ca 40°C and the lower contact to ca 10°C, resulting in a sample temperature of ca 25°C. The A and B components of the adhesive were mixed with a static mixer when applied from a manual cartridge system. The results are listed in Table 2.
  • Lap shear strength was measured according to according to DIN EN 1465:2009. e-coated steel substrates (140 x 25 mm, 0.8 mm thick) were used. The substrates were cleaned with isopropanol before use. Parts (A) and (B) were mixed 1 :1 by volume, and the resulting adhesive was applied on one substrate, before the second substrate was joined within 5 minutes. The thickness was adjusted to 1 .4 mm, the overlap area was 25 mm x 25 mm. The material was allowed to cure and rested for 7 days at 23°C, 50 % relative humidity before the lap shear tests were performed.
  • Comparative Examples CE1 and CE2 which lack the aromatic epoxy resin (a2) and the epoxy silane (a3) have low press-in force, unacceptably low lap shear strengths and very high levels of adhesive failure.
  • Comparative Examples CE3 and CE4 which have the aromatic epoxy resin (a2), but lack the epoxy silane (a3) also have unacceptably low lap shear strengths, and CE3 has a high level of adhesive failure.
  • Comparative Example CE5, which lacks the aromatic epoxy resin (a2), but has the epoxy silane (a3) has an unacceptably low lap shear strength, and high level of adhesive failure.
  • Examples 1 and 2 which are representative of the adhesives of the invention have higher thermal conductivities, excellent lap shear strengths, and 100% cohesive failure.

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Abstract

L'invention concerne un matériau d'interface thermique à deux composants.
PCT/US2021/049615 2020-09-14 2021-09-09 Matériau d'interface thermique WO2022056096A1 (fr)

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KR1020237008862A KR20230069928A (ko) 2020-09-14 2021-09-09 열 계면 재료
US18/025,545 US20230323174A1 (en) 2020-09-14 2021-09-09 Thermal interface material
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022235802A1 (fr) * 2021-05-05 2022-11-10 Dow Global Technologies Llc Matériaux d'interface thermique
WO2023183272A1 (fr) * 2022-03-22 2023-09-28 Ddp Specialty Electronic Materials Us, Llc Adhésif structural thermoconducteur à deux composants
WO2024015165A1 (fr) * 2022-07-14 2024-01-18 Ddp Specialty Electronic Materials Us, Llc Composition adhésive
WO2024076408A1 (fr) * 2022-10-06 2024-04-11 Ddp Specialty Electronic Materials Us, Llc Composition adhésive à deux composants

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KR20230069928A (ko) 2023-05-19

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